Patent GB-604284-A (GB)
Title: A process of polymerising esters of unsaturated alcohols
IPC: C08F28/00
Filed: 1945-01-16
Abstract: Vinyl and/or allyl type diesters of sulphonyl, containing dicarboxylic acids HOOC-R1-SO2-R2-COOH where R1 and R2 are divalent hydrocarbon radicals, which may contain halogen, hydroxyl, alkoxy, oxygen, nitrogen or NH = substituents, or partial polymers or copolymers are polymerized by heating alone or with another polymerizable unsaturated organic compound.  Preferably the heating is continued to obtain an infusible resin.  Vinyl type alcohols specified are vinyl alcohol, propen-1-ol-1, buten-1-ol-1, cyclohexen-1-ol-1, and cyclopenten-1-ol-1, and allyl type alcohols specified are allyl, methallyl, ethallyl, chlorallyl alcohols, buten-1-ol-3, penten-1-ol-3, hexen-1-ol-3, 3-methyl-buten-1-ol-3, 3-methyl-penten-1-ol-3, 2-methyl-buten-1-ol-3, 2-methyl-penten-1-ol-3, 2,3-dimethyl buten-1-ol-3, hepten-1-ol-3, 4 - methyl - hexen - 1 - ol - 3, 5 - methyl hexen-1 - ol - 3, 4,41 - dimethyl - penten - 1 - ol - 3, octen - 1 - ol - 3, 6 - methyl - hepten - 1 - ol - 3, 4 - methyl - hepten - 1 - ol - 3, 4,41 - dimethyl - hexen - 1 - ol - 3, 3 - phenyl - propen - 1 - ol - 3, 3 - tolyl - propen - 1 - ol - 3, 3 - xylyl - propen - 1 - ol - 3, 4 - phenyl - buten - 1 - ol - 3, 4 - tolyl-buten - 1 - ol - 3, 4 - xylyl - buten - 1 - ol - 3, 3 - naphthyl - propen - 1 - ol - 3, 4 - chloro - buten - 1 - ol - 3, pentadien - 1,4 - ol - 3, hexen-1 - yn - 5 - ol - 3, 2 - methyl - penten - 1 - yn - 4 - ol-3, 2,5-dimethyl-hexadien-1,5-ol-4, erotyl, cinnamyl and tiglyl alcohols, 3-chloro-buten-2-ol-1, hexadien-2,4-ol-1, hexadien-2,5-ol-1, butadien - 2,3 - ol - 1, hexadien - 2,4 - ol - 1, 2 - methyl - hexen - 2 - ol - 1, 2 - methyl - penten-2 - ol - 1, 3,7 - dimethyl - octadien - 2,7 - ol -1, cyclopenten - 2 - ol - 1, and cyclohexen - 2 - ol-1.  Esters specified are dially, vinyl-allyl, methallylallyl, dimethallyl and dichlorallyl esters of sulphonyl diglycollic acid, diallyl, vinyl-allyl, and dimethallyl esters of b ,b 1-sulphonyl dihydracrylic acid, vinyl-allyl ester of carboxymethyl sulphonyl-b -propionic acid, diallyl ester of b ,b 1-sulphonyl dibutyric acid and diallyl ester of 4.21-sulphonyldihexahydrobenzoic acid.  Other polymerizable compounds such as styrene, vinyl halides, vinylidene halides, vinyl esters of carboxylic acids, methyl acrylate and methacrylate, allyl halides, unsaturated alkyd resins, allyl esters of carboxylic acids, vinyl, allyl and methallyl esters of phosphoric acid, and ortho acids of silicon and boron, butadiene, chlorobutadiene, isoprene, pentadienes, hexadienes, and diallyl diglycollate, may be added.  The copolymerization can be achieved by mixing the partial polymers and further polymerizing. Catalysts such as acetyl, benzoylacetyl, lauryl, dibutyryl, and succinoyl peroxides, sodium and barium peroxides and t-alkyl hydroperoxides, peracetic or perphthalic acids, perborates, persulphates, ozone, and oxygen or the peroxides or ozonides of the monomers may be present.  Mixed catalysts may be used.  Mass, emulsion or solution methods may be used under reduced or super-pressure using an inert gas if desired.  Fibres may be coated to make laminates or the products mixed with cellulose derivatives, alkyd, urea-aldehyde or phenol-aldehyde resins, polyamides or polyester-amides, dyes, pigments, natural resins and fillers.  Films may be made from the products.  Specification 577,841 is referred to.ALSO:Vinyl and/or allyl type diesters of sulphonyl containing dicarboxylic acids HOOC-R1-SO2-R2-COOH, where R1 and R2 are divalent hydrocarbon radicals, which may contain halogen, hydroxyl, alkoxy, oxygen, nitrogen or NH=substituents, or partial polymers or copolymers are prepared by reacting the metal salt of an acid with halide of the appropriate alcohol, or the halide of an acid with a metallic alcoholate, by acid exchange, ester exchange, or ester interchange, or the acid may be reacted with acetylene in the presence of a mercuric salt, or a mixed ester may be obtained by reacting an acid ester of one unsaturated alcohol with, say, vinyl acetate in the presence of a mercuric salt.  Esters specified are diallyl, vinyl-allyl, methallyl allyl, dimethallyl and dichlorallyl esters of sulphonyl diglycollic acid, diallyl, vinyl allyl and dimethallyl esters of b b 1-sulphonyl dihydracrylic acid, vinyl allyl ester of carboxymethyl sulphonyl-b -propionic acid, diallyl ester of b b 1-sulphonyl dibutyric acid and diallyl ester of 4.21 - sulphonyldihexahydrobenzoic acid.  Specification 577,841 is referred to.